GB859489A - Improvements in and relating to modified polyethylene terephthalate - Google Patents
Improvements in and relating to modified polyethylene terephthalateInfo
- Publication number
- GB859489A GB859489A GB31644/58A GB3164458A GB859489A GB 859489 A GB859489 A GB 859489A GB 31644/58 A GB31644/58 A GB 31644/58A GB 3164458 A GB3164458 A GB 3164458A GB 859489 A GB859489 A GB 859489A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- give
- polyethylene terephthalate
- dimethyl
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 polyethylene terephthalate Polymers 0.000 title abstract 6
- 229920000139 polyethylene terephthalate Polymers 0.000 title abstract 5
- 239000005020 polyethylene terephthalate Substances 0.000 title abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- AOFRNZNXMCOXHP-UHFFFAOYSA-N 2-(2-carboxyphenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C(O)=O AOFRNZNXMCOXHP-UHFFFAOYSA-N 0.000 abstract 1
- WPYCHBBETVULOT-UHFFFAOYSA-N 3-(3-benzoyloxypropylsulfonyl)propyl benzoate Chemical compound C(C1=CC=CC=C1)(=O)OCCCS(=O)(=O)CCCOC(C1=CC=CC=C1)=O WPYCHBBETVULOT-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 abstract 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 abstract 1
- NXMNIHPHNSDPTN-UHFFFAOYSA-N didodecyl(oxo)tin Chemical compound CCCCCCCCCCCC[Sn](=O)CCCCCCCCCCCC NXMNIHPHNSDPTN-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 abstract 1
- 229940069446 magnesium acetate Drugs 0.000 abstract 1
- 235000011285 magnesium acetate Nutrition 0.000 abstract 1
- 239000011654 magnesium acetate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 1
- 229960001860 salicylate Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 1
- LHHPEAQVCCPLBC-UHFFFAOYSA-N tributyltin;hydrate Chemical compound O.CCCC[Sn](CCCC)CCCC LHHPEAQVCCPLBC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
A polyethylene terephthalate is modified to give it improved dyeability by including in its molecule a minor proportion of structural units having the formula: <FORM:0859489/IV(a)/1> where R is an alkylene radical containing 1-5 carbon atoms. The modified polyethylene terephthalate is made by heating a mixture of ethylene glycol, a dialkyl terephthalate and a sulphone dicarboxylic ester of formula: <FORM:0859489/IV(a)/2> (where R1 is an alkyl radical) at 100 DEG -200 DEG C. to effect ester interchange and then polymerizing the resulting glycol esters by heating at 200 DEG -300 DEG C. Catalysts for the reaction are calcium, sodium, magnesium acetate, dibutyl tin oxide, tributyl tin hydroxide, dilauryl tin oxide, dibutyl tin dichloride or the borate, salicylate, benzoate, carbonate or acetate of lead. Examples describe the manufacture of modified polyethylene terephthalates from ethylene glycol, dimethyl terephthalate and either dimethyl 4, 41-[sulphonylbis-(trimethylene)] dibenzoate or dimethyl 4, 41-sulphonylditoluate. Specification 578,079 is referred to.ALSO:Diesters of formula : <FORM:0859489/IV(b)/1> where R is an alkylene radical containing 1-5 carbon atoms and R1 is an alkyl radical which forms an alcohol boiling at below about 200 DEG C. are made by the following series of reactions :-(1) An aralkyl chloride of formula Cl R C6 H5 is reacted with acetyl chloride in the presence of aluminium chloride as a catalyst and carbon disulphide as the reaction medium to give (2) the corresponding acetophenone of formula Cl R C6H4CO CH3 which is oxidised with alkaline hyporbromite solution and acidified with hydrochloric acid to give (3) the corresponding benzoic acid of formula Cl R C6H4 COOH which is reacted with sodium sulphide to form (4) the 4, 41-(thiodialkylene) dibenzoic acid of formula HOOC C6H4RSR C6H4COOH which is oxidised with peracetic acid to give (5) the sulphonyl dibenzoic acid formula HOOC C6H4R SO2 R C6 H4COOH which is esterified with an alcohol of formula R1OH to give (6) the desired product. The diesters are used to modify polyethylene terephthalate, (see Group IV(a)).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1215665XA | 1957-10-07 | 1957-10-07 | |
| US859489XA | 1957-10-07 | 1957-10-07 | |
| US688431A US3032534A (en) | 1957-10-07 | 1957-10-07 | Sulfone-modified polyethylene terephthalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB859489A true GB859489A (en) | 1961-01-25 |
Family
ID=27375165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31644/58A Expired GB859489A (en) | 1957-10-07 | 1958-10-03 | Improvements in and relating to modified polyethylene terephthalate |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1215665A (en) |
| GB (1) | GB859489A (en) |
-
1958
- 1958-10-03 GB GB31644/58A patent/GB859489A/en not_active Expired
- 1958-10-03 FR FR775879A patent/FR1215665A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1215665A (en) | 1960-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2319576A (en) | Peroxidized ester | |
| GB849109A (en) | Method of preparing esters | |
| GB793907A (en) | Linear polyesters of terephthalic acid and a process of producing them | |
| US2393327A (en) | Esters | |
| GB949085A (en) | Catalyst system for use in the manufacture of linear fibre and film-forming polyesters | |
| GB997398A (en) | Phosphorus-containing fibre-forming polyesters | |
| GB859489A (en) | Improvements in and relating to modified polyethylene terephthalate | |
| GB955232A (en) | Improvements in or relating to the preparation of macromolecular polymethylene terephthalates | |
| GB978172A (en) | Improvements in or relating to the preparation of diesters of phthalic acids | |
| GB1511429A (en) | Ethylene glycol terephthalate production | |
| GB1416446A (en) | Sperm oil | |
| GB1024487A (en) | A new bicyclic glycol and polyesters made therefrom | |
| GB835442A (en) | Glycol esters of terephthalic acid | |
| GB775316A (en) | Polyglycol terephthalates and isophthalates | |
| GB1100753A (en) | Improvements in polyesterification catalysts | |
| US2867650A (en) | Process for the preparation of monodiol esters of terephthalic acid | |
| GB650002A (en) | New or improved resinous polyesters and method for their manufacture | |
| GB1008846A (en) | Phosphorus-containing unsaturated polyesters | |
| GB651762A (en) | Improvements in and relating to the production of polymeric esters | |
| GB773538A (en) | Improvements in the production of linear polyesters | |
| GB1005996A (en) | Process for the production of optically brightened polyesters of terephthalic acid | |
| GB836544A (en) | Production of benzoate esters | |
| GB662656A (en) | Esters of sulphonyl alcohols and compositions containing such esters | |
| GB649655A (en) | Solutions of aromatic polyesters | |
| GB762690A (en) | Improved process for the recovery of synthetic polyester scrap |